Bill Murray has had quite a journey. He's gone from Chevy Chase's SNL replacement to the leading snark-master (before blogs made snark hip) to a serious actor working with the best directors of our time. But while you may count yourself as a Murray fan, there are probably roles you've missed. Do you remember him as a greedy underworld emperor in a certain fantastical kids' flick? As a mafia boss-slash-aspiring comedian vying for Uma Thurman's affections? Read on.

1. City of Ember (2008)
Audiences virtually ignored this adaptation of the popular kids novel, and it was their loss: Murray gives a nuanced, sad, brilliant turn as the mayor of a city buried far below the Earth's surface. A scene towards the end finds Murray, locked in a room, all alone, falling asleep gorged on canned fruit, perfectly encapsulating everything good about his performance.

2. Broken Flowers (2005)
Murray's second collaboration with Jim Jarmusch finds the actor as an aging Don Juan looking to reunite with his long lost son. Murray's later career is categorized more by silence than the jabber mouth his early comedy showcased, and Broken Flowers showcases his late-in-life style at its pinnacle -- at least for now...

3. Coffee and Cigarettes (2003)
Murray's first collaboration with Jarmusch was this gritty short film anthology. Murray, in probably his strangest role ever, stars in the title film, in which he has a conversation with GZA and RZA of the Wu-Tang Clan about the dangers of smoking and caffeine intake. Murray wittily discussing life and vices with two rappers is probably the closest America's moviegoing audience has gotten to truly knowing what the man himself is like.

4. The Man Who Knew Too Little (1997)
A parody of Hitchcockian "normal man in over their head" stories, but nothing like the Michael Douglas movie The Game, TMWK2L finds Murray thinking he's participating in an interactive theater performance as a hitman... When he's actually been mistaken by international spies as a notorious hitman. Murray's cluelessness in the movie harkens back to the "dumb man" sort he hasn't really played since Caddyshack and What About Bob. Also, it's easily the funniest Bill Murray performance most people have never seen.

5. Mad Dog and Glory (1993)
You wouldn't think, in a movie showcasing Bill Murray and Robert De Niro competing for Uma Thurman's affections, that Murray would be the dominant member of the trio. But as a mafia boss/aspiring stand-up comedian, Murray dominates the meek De Niro... And ends up losing Uma Thurman in the process. This marked the beginning of Murray's "funny mixed with sad" phase, and can also be read as a deconstruction of his (somewhat negative) feelings towards comedy.

Honorable Mentions:

1. Osmosis Jones (2001): As the literal vehicle for the animated white blood cells and medicine running through his body, Murray fleshes out the part of "sick guy" admirably, and makes us laugh through the pain.

2. Hamlet (2000): Poor, doomed Polonius. Murray is a the stand-out performance in a modern updating of the play starring Ethan Hawke as the titular Dane. Showy without showing off, Murray steals the show.

3. Cradle Will Rock (1999): You may have missed him in the over-packed ensemble cast of this movie, but Murray perfectly portrays ventriloquist Tommy Circkshaw in Tim Robbins period piece, once again with his now trademark mix of sadness and humor.

4. Wild Things (1998)
Murray plays a shyster lawyer working for (and against) the Wild Things of the title, and literally gets the last word in the movie. In a movie drenched in Florida sweat, Murray is the slimiest.

5. Little Shop of Horrors (1986): It's hard to steal a scene from Steve Martin, but Murray does so as the only patient able to frustrate Martin's pain-loving dentist. Not only that, but he once again manages to steal the show without singing a single note.

Rank your favorites among AMCtv.com's Top 20 Bill Murray Movies list now!